Salicylic-acid methylene acetate and process of making same.



nsnnn srrrns PATENT .ornron g rninnnronwmnnmr SAMUEL VALENTINER, orLEIPSIC, GERMANY.

SALlCYLIC-ACID METHYLENE AQETATE AND PROCESS OF MAKING SAME.

Specification of Letters intent.

Application filed May 12, 1905 Serial No.,2 60,123. (Specimens) PatentedFeb. 6, 1906.

prove'mentir Salicylic-Acid Methylene Acetate and. Process of Makin theSame, of which the following is a speoi cation.

- A'cetyl salicylic acid havin' a melting point of 135 centigrade, freeI om salicylic acid and acetic acid, is mixed with half its weight (onemolecule) of formaldeh de solution of fOrty-per-cent. strength and eatedin a flask in a sand-bathuntil the whole is dis solved. The flask isthen emptied into a porcelain basin, the crystal cakes formed on coolingare comminuted, and the entire mass recrystallized from water. The newbodyso obtained is soluble with difiiculty in cold water, readilysoluble in warm water and in .alco- 5 I 'twenty grams, according to theconstitution of the patient suffering from gout hol, but somewhat lesssoluble in other. It crystallizes in small needles and has a feeble butcharacteristic smell'of the salicylic-acid esters and melts at 108centig'rade. mentary analysis gave the following values: 0.1610 rams ofthe substance 'elded 0.0725 grams fl O and 0.3375 grams 0,:

Found. Calculated from the formula (3, 11, 0

4.76 per cent.

H. 5.00 per cent. C. 57.14 per cent.

57.02 per cent.

The new body has thus the formula O l-L 0 and the reaction must beaccording to the following equation:

o-oo-cn, 4 OOH,-O-CO4-CH,, coon coon It is known that acid anhydridereact with aldehydes in the above manner; but.it was.

col-l1ke methylene acetate. Acetyl salicy acid, on the other hand, withits acid ester,

group, gives no coloration withiron.

If to a trace of the salio lie-acid methylene acetate be added one-hatcubiccentimeter Elef Witnesses:

of 0.1per-'cent.phloroglucin solution and then somedro s of potash lye,there is produced a slightrown coloration.

the coloration becomes very distinct. T

appears to be due to the fact that the saponification of the abovecompound takes place very slowly. If the acetate be boiled some timewith ammoniacal silver-nitrate solution, the aldehyde "silver-mirror isformed in the glass.- Acet'yl salicylioacid treated in the same waygives nos1lvermirr0r. The new composition of matter is therefore anorganic chemical product formed by reacting on one molecule of acetylsalicylic acid with one molecule of formaldehyde and is designed, byreason of its valuable therapeutical properties, tobe used as aninternal medicine for dissolving the sediments of uric acid. It isadministered in doses of five to or rheumaof formalde yde one moleculeon two mole f cules of salic lic acid and having the meltingpoint of 245centigrade, (United States Patent No. 706,354, methylene disalicylicacid,)

When the same has been allowed to stand some days, s

which intermediate product if afterward acetylated has a meltingpoint of145 centigrade, (United States atent N6. 7 70,17 8 methylene di-acetodi-salicyl acid.) Both last-named dproducts are perfectly insoluble inwater an contain less formaldehyde than my roduct.

' at I claim, and desire to secure by Let- 'ters Patent of the UnitedStates, is

1. The herein-described method of produc ing' salicylic-acid methyleneacetate consistmg in reacting on acetyl salicylic acid withformaldehyde.

2. The new composition of matter having the formula O l-1, 0constituting salicylicj acid methylene acetate, solublein water andmelting at 108, as described.

In testimony whereof I have signed my name to this specification in thepresence of two subscribing witnesses.

FRIEDRIGH WILHELM. SAMUEL VAhENTINER..

RUno Pn Felons, Sou'rr'mnn P. WARNER.

